# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_3a
_database_code_depnum_ccdc_archive 'CCDC 2225069'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_PLAT342_3a                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02261 Ang.  
RESPONSE: The crystals were 
weakly diffracting, even with 
prolonged exposure times, 
which made it difficult to 
collect the high angle data 
to a sufficient quality.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 I N3 O4'
_chemical_formula_sum            'C20 H22 I N3 O4'
_chemical_formula_weight         495.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.0497(6)
_cell_length_b                   10.5607(8)
_cell_length_c                   18.3987(13)
_cell_angle_alpha                90
_cell_angle_beta                 106.167(4)
_cell_angle_gamma                90
_cell_volume                     2062.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5091
_cell_measurement_temperature    170
_cell_measurement_theta_max      28.700
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.742
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0966 before and 0.0795 after correction. The Ratio of minimum to maximum transmission is 0.7163. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13537
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.188
_diffrn_reflns_theta_min         1.919
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.607
_reflns_Friedel_fraction_full    0.678
_reflns_Friedel_fraction_max     0.682
_reflns_number_gt                4185
_reflns_number_total             6319
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 
;
 Flack x determined using 1272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         6319
_refine_ls_number_restraints     337
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.2681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C76 \\sim C77 \\sim C78 \\sim C78A: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
O74 \\sim O74A \\sim O75 \\sim O75A \\sim N65 \\sim N65A \\sim C66 \\sim C66A
\\sim C67 \\sim C67A \\sim C68 \\sim C68A \\sim C69 \\sim C69A \\sim C70 \\sim
C70A \\sim C71 \\sim C71A \\sim C72 \\sim C72A \\sim C73 \\sim C73A: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C73A) = Uanis(C66A)
Uanis(C66) = Uanis(C73)
3. Others
 Sof(O74A)=Sof(O75A)=Sof(N65A)=Sof(C66A)=Sof(C67A)=Sof(C72A)=Sof(C73A)=
 Sof(H64A)=Sof(C68A)=Sof(H68A)=Sof(C69A)=Sof(H69A)=Sof(C70A)=Sof(H70A)=
 Sof(C71A)=Sof(H71A)=Sof(H76)=Sof(C78A)=Sof(H78D)=Sof(H78E)=Sof(H78F)=1-FVAR(1)
 Sof(O74)=Sof(O75)=Sof(N65)=Sof(H64)=Sof(C66)=Sof(C67)=Sof(C68)=Sof(H68)=
 Sof(C69)=Sof(H69)=Sof(C70)=Sof(H70)=Sof(C71)=Sof(H71)=Sof(C72)=Sof(C73)=
 Sof(H76A)=Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(H78C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C26(H26), C64(H64), C64(H64A), C76(H76), C76(H76A)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20), C21(H21),
 C52(H52), C53(H53), C55(H55), C56(H56), C68(H68), C68A(H68A), C69(H69),
 C69A(H69A), C70(H70), C70A(H70A), C71(H71), C71A(H71A)
4.c Fitted pentagon refined as free rotating group:
 N65A(C66A,C67A,C72A,C73A)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C),
 C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C77(H77A,H77B,H77C), C78(H78A,H78B,
 H78C), C78A(H78D,H78E,H78F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.09254(10) 0.67049(7) 0.38620(6) 0.0435(4) Uani 1 1 d . . . . .
O11 O 0.1696(10) 0.7060(12) 0.2892(6) 0.048(4) Uani 1 1 d . . . . .
O13 O 0.2630(13) 0.5143(15) 0.3022(8) 0.063(4) Uani 1 1 d . . . . .
O24 O 0.4168(8) 0.8056(9) 0.2526(5) 0.049(3) Uani 1 1 d . . . . .
O25 O 0.0413(8) 0.7702(12) 0.0705(5) 0.054(3) Uani 1 1 d . . . . .
N1 N -0.0101(13) 0.6427(18) 0.4754(7) 0.043(5) Uani 1 1 d . . . . .
N7 N -0.2289(12) 0.6091(17) 0.6244(8) 0.044(4) Uani 1 1 d . . . . .
N15 N 0.2326(11) 0.7516(13) 0.1613(6) 0.035(3) Uani 1 1 d . . . . .
C2 C 0.0120(15) 0.7179(16) 0.5363(9) 0.036(5) Uani 1 1 d . . . . .
H2 H 0.0786 0.7778 0.5448 0.044 Uiso 1 1 calc R . . . .
C3 C -0.0584(14) 0.7107(19) 0.5862(9) 0.044(6) Uani 1 1 d . . . . .
H3 H -0.0440 0.7689 0.6271 0.052 Uiso 1 1 calc R . . . .
C4 C -0.1534(15) 0.6164(18) 0.5775(9) 0.034(5) Uani 1 1 d . . . . .
C5 C -0.1728(18) 0.540(2) 0.5143(10) 0.046(5) Uani 1 1 d . . . . .
H5 H -0.2354 0.4757 0.5054 0.055 Uiso 1 1 calc R . . . .
C6 C -0.1030(15) 0.5563(19) 0.4646(10) 0.040(5) Uani 1 1 d . . . . .
H6 H -0.1204 0.5047 0.4206 0.048 Uiso 1 1 calc R . . . .
C8 C -0.2148(14) 0.693(2) 0.6884(8) 0.050(6) Uani 1 1 d . . . . .
H8A H -0.2928 0.6930 0.7040 0.074 Uiso 1 1 calc GR . . . .
H8B H -0.1974 0.7791 0.6741 0.074 Uiso 1 1 calc GR . . . .
H8C H -0.1449 0.6638 0.7306 0.074 Uiso 1 1 calc GR . . . .
C9 C -0.3123(15) 0.5022(18) 0.6209(10) 0.052(6) Uani 1 1 d . . . . .
H9A H -0.3532 0.4811 0.5678 0.078 Uiso 1 1 calc GR . . . .
H9B H -0.3766 0.5239 0.6463 0.078 Uiso 1 1 calc GR . . . .
H9C H -0.2636 0.4292 0.6461 0.078 Uiso 1 1 calc GR . . . .
C12 C 0.2232(15) 0.609(2) 0.2685(10) 0.049(5) Uani 1 1 d . . . . .
C14 C 0.2173(12) 0.6199(14) 0.1821(7) 0.041(4) Uani 1 1 d . . . . .
H14 H 0.1282 0.5985 0.1546 0.049 Uiso 1 1 calc R . . . .
C16 C 0.3285(15) 0.8338(17) 0.1997(10) 0.042(5) Uani 1 1 d . . . . .
C17 C 0.2976(15) 0.9611(15) 0.1635(9) 0.037(4) Uani 1 1 d . . . . .
C18 C 0.3651(12) 1.0726(14) 0.1737(8) 0.040(3) Uani 1 1 d . . . . .
H18 H 0.4447 1.0799 0.2103 0.048 Uiso 1 1 calc R . . . .
C19 C 0.3127(15) 1.170(2) 0.1293(9) 0.052(4) Uani 1 1 d . . . . .
H19 H 0.3576 1.2481 0.1356 0.062 Uiso 1 1 calc R . . . .
C20 C 0.1977(15) 1.1650(19) 0.0752(9) 0.053(4) Uani 1 1 d . . . . .
H20 H 0.1655 1.2376 0.0457 0.064 Uiso 1 1 calc R . . . .
C21 C 0.1296(13) 1.0535(17) 0.0642(8) 0.051(4) Uani 1 1 d . . . . .
H21 H 0.0497 1.0474 0.0277 0.061 Uiso 1 1 calc R . . . .
C22 C 0.1828(17) 0.951(2) 0.1084(9) 0.042(4) Uani 1 1 d . . . . .
C23 C 0.1382(15) 0.820(2) 0.1074(8) 0.048(5) Uani 1 1 d . . . . .
C26 C 0.2966(15) 0.5216(18) 0.1542(10) 0.050(5) Uani 1 1 d . . . . .
H26 H 0.2733 0.4359 0.1692 0.060 Uiso 1 1 calc R . . . .
C27 C 0.4420(12) 0.5383(15) 0.1888(10) 0.057(5) Uani 1 1 d . . . . .
H27A H 0.4675 0.6218 0.1749 0.086 Uiso 1 1 calc GR . . . .
H27B H 0.4865 0.4723 0.1690 0.086 Uiso 1 1 calc GR . . . .
H27C H 0.4630 0.5315 0.2440 0.086 Uiso 1 1 calc GR . . . .
C28 C 0.2664(15) 0.5244(17) 0.0691(8) 0.067(5) Uani 1 1 d . . . . .
H28A H 0.1793 0.4966 0.0470 0.101 Uiso 1 1 calc GR . . . .
H28B H 0.3238 0.4675 0.0527 0.101 Uiso 1 1 calc GR . . . .
H28C H 0.2765 0.6108 0.0524 0.101 Uiso 1 1 calc GR . . . .
I2 I 0.40381(10) 0.75817(8) 0.61964(6) 0.0479(5) Uani 1 1 d . . . . .
O61 O 0.3095(11) 0.7151(15) 0.7098(7) 0.062(5) Uani 1 1 d . . . . .
O63 O 0.2044(13) 0.8929(17) 0.6871(9) 0.073(5) Uani 1 1 d . . . . .
O74 O 0.417(5) 0.693(3) 0.888(3) 0.065(10) Uani 0.63(2) 1 d . U P A 1
O74A O 0.419(7) 0.739(5) 0.885(5) 0.045(10) Uani 0.37(2) 1 d . U P A 2
O75 O 0.038(4) 0.523(4) 0.761(2) 0.067(10) Uani 0.63(2) 1 d . U P A 1
O75A O 0.063(8) 0.503(8) 0.783(4) 0.066(13) Uani 0.37(2) 1 d . U P A 2
N51 N 0.5048(12) 0.7852(16) 0.5327(8) 0.040(4) Uani 1 1 d . . . . .
N57 N 0.7191(13) 0.8200(17) 0.3804(8) 0.048(5) Uani 1 1 d . . . . .
N65 N 0.219(5) 0.638(4) 0.820(3) 0.045(6) Uani 0.63(2) 1 d . U P A 1
N65A N 0.221(7) 0.649(6) 0.825(5) 0.046(7) Uani 0.37(2) 1 d . U P A 2
C66A C 0.347(7) 0.645(4) 0.872(4) 0.050(6) Uani 0.37(2) 1 d G U P A 2
C67A C 0.375(4) 0.517(5) 0.895(3) 0.047(7) Uani 0.37(2) 1 d G U P A 2
C72A C 0.266(5) 0.443(4) 0.862(3) 0.054(8) Uani 0.37(2) 1 d G U P A 2
C73A C 0.171(4) 0.525(7) 0.819(4) 0.050(6) Uani 0.37(2) 1 d G U P A 2
C52 C 0.5976(16) 0.8729(19) 0.5431(11) 0.049(6) Uani 1 1 d . . . . .
H52 H 0.6146 0.9251 0.5869 0.059 Uiso 1 1 calc R . . . .
C53 C 0.6679(15) 0.889(2) 0.4930(9) 0.041(5) Uani 1 1 d . . . . .
H53 H 0.7286 0.9555 0.5013 0.049 Uiso 1 1 calc R . . . .
C54 C 0.6516(17) 0.8095(19) 0.4294(11) 0.048(6) Uani 1 1 d . . . . .
C55 C 0.5488(15) 0.7215(18) 0.4187(9) 0.043(6) Uani 1 1 d . . . . .
H55 H 0.5274 0.6687 0.3752 0.051 Uiso 1 1 calc R . . . .
C56 C 0.4824(15) 0.714(2) 0.4701(10) 0.052(7) Uani 1 1 d . . . . .
H56 H 0.4159 0.6537 0.4614 0.063 Uiso 1 1 calc R . . . .
C58 C 0.8104(15) 0.920(2) 0.3857(10) 0.062(7) Uani 1 1 d . . . . .
H58A H 0.8864 0.9013 0.4266 0.093 Uiso 1 1 calc GR . . . .
H58B H 0.7744 1.0007 0.3964 0.093 Uiso 1 1 calc GR . . . .
H58C H 0.8322 0.9270 0.3377 0.093 Uiso 1 1 calc GR . . . .
C59 C 0.7048(15) 0.735(3) 0.3155(9) 0.069(8) Uani 1 1 d . . . . .
H59A H 0.6724 0.6527 0.3267 0.103 Uiso 1 1 calc GR . . . .
H59B H 0.7868 0.7225 0.3058 0.103 Uiso 1 1 calc GR . . . .
H59C H 0.6456 0.7718 0.2707 0.103 Uiso 1 1 calc GR . . . .
C62 C 0.2354(16) 0.7980(18) 0.7233(9) 0.042(5) Uani 1 1 d . . . . .
C64 C 0.1686(11) 0.7569(16) 0.7825(7) 0.046(3) Uani 1 1 d . . . . .
H64 H 0.0792 0.7390 0.7538 0.056 Uiso 0.63(2) 1 calc R . P A 1
H64A H 0.0796 0.7355 0.7545 0.056 Uiso 0.37(2) 1 calc R . P A 2
C66 C 0.341(4) 0.614(3) 0.867(3) 0.047(4) Uani 0.63(2) 1 d . U P A 1
C67 C 0.335(4) 0.473(4) 0.882(2) 0.045(6) Uani 0.63(2) 1 d . U P A 1
C68 C 0.433(3) 0.400(3) 0.9247(19) 0.058(7) Uani 0.63(2) 1 d . U P A 1
H68 H 0.5133 0.4363 0.9463 0.069 Uiso 0.63(2) 1 calc R . P A 1
C68A C 0.480(4) 0.458(5) 0.945(3) 0.045(8) Uani 0.37(2) 1 d . U P A 2
H68A H 0.5516 0.5071 0.9708 0.054 Uiso 0.37(2) 1 calc R . P A 2
C69 C 0.413(3) 0.279(4) 0.935(2) 0.060(7) Uani 0.63(2) 1 d . U P A 1
H69 H 0.4764 0.2290 0.9681 0.072 Uiso 0.63(2) 1 calc R . P A 1
C69A C 0.480(5) 0.332(5) 0.958(3) 0.054(8) Uani 0.37(2) 1 d . U P A 2
H69A H 0.5559 0.2921 0.9856 0.065 Uiso 0.37(2) 1 calc R . P A 2
C70 C 0.299(3) 0.225(4) 0.8980(19) 0.066(7) Uani 0.63(2) 1 d . U P A 1
H70 H 0.2872 0.1370 0.9046 0.079 Uiso 0.63(2) 1 calc R . P A 1
C70A C 0.362(5) 0.255(7) 0.930(4) 0.056(9) Uani 0.37(2) 1 d . U P A 2
H70A H 0.3595 0.1670 0.9411 0.067 Uiso 0.37(2) 1 calc R . P A 2
C71 C 0.204(3) 0.291(4) 0.8530(19) 0.060(8) Uani 0.63(2) 1 d . U P A 1
H71 H 0.1286 0.2503 0.8261 0.072 Uiso 0.63(2) 1 calc R . P A 1
C71A C 0.262(5) 0.318(6) 0.889(3) 0.065(7) Uani 0.37(2) 1 d . U P A 2
H71A H 0.1823 0.2766 0.8768 0.077 Uiso 0.37(2) 1 calc R . P A 2
C72 C 0.219(3) 0.423(4) 0.846(2) 0.052(6) Uani 0.63(2) 1 d . U P A 1
C73 C 0.147(4) 0.532(5) 0.806(3) 0.047(4) Uani 0.63(2) 1 d . U P A 1
C76 C 0.163(2) 0.8652(19) 0.8390(11) 0.059(6) Uani 1 1 d . U . . .
H76 H 0.2496 0.9032 0.8539 0.071 Uiso 0.37(2) 1 calc R . P A 1
H76A H 0.2462 0.8921 0.8735 0.071 Uiso 0.63(2) 1 calc R . P A 2
C77 C 0.079(2) 0.967(2) 0.8031(12) 0.097(7) Uani 1 1 d . U . . .
H77A H 0.1090 1.0041 0.7624 0.145 Uiso 1 1 calc GR . . . .
H77B H 0.0775 1.0321 0.8407 0.145 Uiso 1 1 calc GR . . . .
H77C H -0.0061 0.9331 0.7819 0.145 Uiso 1 1 calc GR . . . .
C78 C 0.142(3) 0.816(3) 0.9115(17) 0.065(9) Uani 0.63(2) 1 d . U P A 1
H78A H 0.2062 0.8502 0.9549 0.098 Uiso 0.63(2) 1 calc GR . P A 1
H78B H 0.1470 0.7231 0.9122 0.098 Uiso 0.63(2) 1 calc GR . P A 1
H78C H 0.0581 0.8418 0.9144 0.098 Uiso 0.63(2) 1 calc GR . P A 1
C78A C 0.059(6) 0.810(6) 0.881(3) 0.085(15) Uani 0.37(2) 1 d . U P A 2
H78D H 0.0918 0.8205 0.9359 0.128 Uiso 0.37(2) 1 calc GR . P A 2
H78E H 0.0431 0.7203 0.8688 0.128 Uiso 0.37(2) 1 calc GR . P A 2
H78F H -0.0202 0.8576 0.8629 0.128 Uiso 0.37(2) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O11 2.213(9) . ?
I1 N1 2.259(11) . ?
O11 C12 1.29(2) . ?
O13 C12 1.20(2) . ?
O24 C16 1.208(18) . ?
O25 C23 1.219(18) . ?
N1 C2 1.34(2) . ?
N1 C6 1.35(2) . ?
N7 C4 1.358(17) . ?
N7 C8 1.45(2) . ?
N7 C9 1.45(2) . ?
N15 C14 1.465(18) . ?
N15 C16 1.40(2) . ?
N15 C23 1.422(19) . ?
C2 C3 1.36(2) . ?
C3 C4 1.42(2) . ?
C4 C5 1.38(2) . ?
C5 C6 1.36(2) . ?
C12 C14 1.58(2) . ?
C14 C26 1.54(2) . ?
C16 C17 1.50(2) . ?
C17 C18 1.379(19) . ?
C17 C22 1.39(2) . ?
C18 C19 1.34(2) . ?
C19 C20 1.38(2) . ?
C20 C21 1.38(2) . ?
C21 C22 1.38(2) . ?
C22 C23 1.46(3) . ?
C26 C27 1.56(2) . ?
C26 C28 1.51(2) . ?
I2 O61 2.238(10) . ?
I2 N51 2.209(12) . ?
O61 C62 1.269(19) . ?
O63 C62 1.20(2) . ?
O74 C66 1.17(6) . ?
O74A C66A 1.26(8) . ?
O75 C73 1.26(6) . ?
O75A C73A 1.22(10) . ?
N51 C52 1.35(2) . ?
N51 C56 1.34(2) . ?
N57 C54 1.324(19) . ?
N57 C58 1.45(2) . ?
N57 C59 1.47(2) . ?
N65 C64 1.46(3) . ?
N65 C66 1.41(3) . ?
N65 C73 1.35(4) . ?
N65A C66A 1.4200 . ?
N65A C73A 1.4200 . ?
N65A C64 1.41(4) . ?
C66A C67A 1.4200 . ?
C67A C72A 1.4200 . ?
C67A C68A 1.42(5) . ?
C72A C73A 1.4200 . ?
C72A C71A 1.41(7) . ?
C52 C53 1.37(2) . ?
C53 C54 1.41(2) . ?
C54 C55 1.44(2) . ?
C55 C56 1.35(2) . ?
C62 C64 1.540(18) . ?
C64 C76 1.56(2) . ?
C66 C67 1.52(5) . ?
C67 C68 1.37(5) . ?
C67 C72 1.38(5) . ?
C68 C69 1.32(5) . ?
C68A C69A 1.35(7) . ?
C69 C70 1.37(4) . ?
C69A C70A 1.50(7) . ?
C70 C71 1.34(4) . ?
C70A C71A 1.34(8) . ?
C71 C72 1.41(5) . ?
C72 C73 1.48(4) . ?
C76 C77 1.45(3) . ?
C76 C78 1.51(3) . ?
C76 C78A 1.66(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 I1 N1 172.6(5) . . ?
C12 O11 I1 114.5(10) . . ?
C2 N1 I1 121.2(12) . . ?
C2 N1 C6 118.8(12) . . ?
C6 N1 I1 119.8(11) . . ?
C4 N7 C8 122.5(16) . . ?
C4 N7 C9 120.8(16) . . ?
C9 N7 C8 115.9(13) . . ?
C16 N15 C14 125.7(14) . . ?
C16 N15 C23 109.9(14) . . ?
C23 N15 C14 123.5(14) . . ?
N1 C2 C3 121.7(16) . . ?
C2 C3 C4 120.4(16) . . ?
N7 C4 C3 122.2(16) . . ?
N7 C4 C5 121.5(17) . . ?
C5 C4 C3 116.1(14) . . ?
C6 C5 C4 120.5(18) . . ?
N1 C6 C5 122.5(17) . . ?
O11 C12 C14 110.3(15) . . ?
O13 C12 O11 130.0(16) . . ?
O13 C12 C14 119.2(18) . . ?
N15 C14 C12 110.8(12) . . ?
N15 C14 C26 115.9(11) . . ?
C26 C14 C12 114.9(13) . . ?
O24 C16 N15 125.6(17) . . ?
O24 C16 C17 127.8(17) . . ?
N15 C16 C17 106.6(15) . . ?
C18 C17 C16 131.2(17) . . ?
C18 C17 C22 120.9(17) . . ?
C22 C17 C16 107.8(15) . . ?
C19 C18 C17 116.6(15) . . ?
C18 C19 C20 124.2(18) . . ?
C19 C20 C21 119.7(18) . . ?
C20 C21 C22 117.1(16) . . ?
C17 C22 C23 108.4(16) . . ?
C21 C22 C17 121.5(19) . . ?
C21 C22 C23 130.1(18) . . ?
O25 C23 N15 121.8(19) . . ?
O25 C23 C22 131.1(19) . . ?
N15 C23 C22 107.1(15) . . ?
C14 C26 C27 113.9(14) . . ?
C28 C26 C14 110.6(14) . . ?
C28 C26 C27 109.0(13) . . ?
N51 I2 O61 175.2(6) . . ?
C62 O61 I2 117.6(11) . . ?
C52 N51 I2 120.1(12) . . ?
C56 N51 I2 122.6(12) . . ?
C56 N51 C52 117.2(14) . . ?
C54 N57 C58 122.0(17) . . ?
C54 N57 C59 123.2(17) . . ?
C58 N57 C59 114.8(14) . . ?
C66 N65 C64 128(4) . . ?
C73 N65 C64 120(4) . . ?
C73 N65 C66 112(3) . . ?
C73A N65A C66A 108.0 . . ?
C64 N65A C66A 123(6) . . ?
C64 N65A C73A 128(6) . . ?
O74A C66A N65A 124(6) . . ?
O74A C66A C67A 128(6) . . ?
N65A C66A C67A 108.00(7) . . ?
C72A C67A C66A 108.0 . . ?
C68A C67A C66A 134(5) . . ?
C68A C67A C72A 118(4) . . ?
C67A C72A C73A 108.0 . . ?
C71A C72A C67A 119(5) . . ?
C71A C72A C73A 132(5) . . ?
O75A C73A N65A 121(7) . . ?
O75A C73A C72A 131(7) . . ?
N65A C73A C72A 108.0 . . ?
N51 C52 C53 122.7(18) . . ?
C52 C53 C54 121.0(18) . . ?
N57 C54 C53 123.2(18) . . ?
N57 C54 C55 122.3(18) . . ?
C53 C54 C55 114.4(15) . . ?
C56 C55 C54 120.4(18) . . ?
N51 C56 C55 124.1(17) . . ?
O61 C62 C64 114.0(15) . . ?
O63 C62 O61 124.6(14) . . ?
O63 C62 C64 120.6(15) . . ?
N65 C64 C62 112(2) . . ?
N65 C64 C76 114(2) . . ?
N65A C64 C62 115(4) . . ?
N65A C64 C76 108(4) . . ?
C62 C64 C76 112.3(14) . . ?
O74 C66 N65 123(4) . . ?
O74 C66 C67 135(4) . . ?
N65 C66 C67 102(3) . . ?
C68 C67 C66 126(4) . . ?
C68 C67 C72 123(4) . . ?
C72 C67 C66 112(3) . . ?
C69 C68 C67 119(4) . . ?
C69A C68A C67A 121(5) . . ?
C68 C69 C70 120(4) . . ?
C68A C69A C70A 121(5) . . ?
C71 C70 C69 123(4) . . ?
C71A C70A C69A 115(6) . . ?
C70 C71 C72 119(4) . . ?
C70A C71A C72A 124(6) . . ?
C67 C72 C71 117(3) . . ?
C67 C72 C73 104(3) . . ?
C71 C72 C73 139(4) . . ?
O75 C73 N65 127(4) . . ?
O75 C73 C72 123(4) . . ?
N65 C73 C72 110(3) . . ?
C64 C76 C78A 102(2) . . ?
C77 C76 C64 112.2(17) . . ?
C77 C76 C78 114.7(18) . . ?
C77 C76 C78A 92(3) . . ?
C78 C76 C64 112.3(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/tert-butylmethylether'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_OHD-4-morpy_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2245212'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 N2 O'
_chemical_formula_sum            'C9 H12 N2 O'
_chemical_formula_weight         164.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7571(4)
_cell_length_b                   7.3863(2)
_cell_length_c                   12.0704(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.521(4)
_cell_angle_gamma                90
_cell_volume                     809.25(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5364
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.9810
_cell_measurement_theta_min      4.8980
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.76a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 0 0 0.0184
-6 0 0 0.0154
-2 3 6 0.0624
1 4 -5 0.0419
1 -5 0 0.0249
2 1 -8 0.0687
-1 5 2 0.0614
-2 0 8 0.0765
-2 -3 6 0.0671
4 -3 2 0.0340
2 4 -3 0.0462

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.8606 0.1411 0.0984 0.0251 0.9976 -0.0646
-5.8606 -0.1411 -0.0984 -0.0251 -0.9976 0.0646
-2.0627 3.0006 6.1013 0.9732 -0.0249 0.2285
0.9041 3.8210 -4.6873 -0.1931 0.0020 0.9812
0.5470 -4.7750 -0.0585 -0.4390 0.0135 -0.8984
2.1376 0.5871 -7.7717 -0.8405 0.0194 0.5415
-1.0439 4.6397 1.8645 0.6344 -0.0181 0.7728
-2.2555 0.3787 7.8091 0.9322 -0.0222 -0.3612
-1.7868 -2.8035 6.3533 0.4767 -0.0596 -0.8770
3.9375 -2.6527 2.2555 0.0199 0.7253 -0.6881
1.6438 4.2974 -3.3653 0.0023 0.1944 0.9809

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_unetI/netI     0.0029
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3052
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.494
_diffrn_reflns_theta_min         4.872
_diffrn_reflns_v_R_equivalents   ?
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  33.00   1.00    3.00    --  -47.93  35.00 -90.00   48
  2  ω    -89.00 -54.00   1.00    3.00    --  -47.93 -35.00 112.00   35
  3  ω     60.00  86.00   1.00    3.00    --   48.87  35.00 -90.00   26
  4  ω   -105.00 -68.00   1.00   12.00    --  -88.36 -35.00 112.00   37
  5  ω   -162.00-109.00   1.00   12.00    --  -88.36 -35.00 112.00   53
  6  ω     86.00 170.00   1.00   12.00    --  107.71  35.00 -90.00   84
  7  ω     -2.00  33.00   1.00    3.00    --  -47.93  19.00  30.00   35
  8  ω   -120.00 -75.00   1.00    3.00    --  -47.93-125.00-150.00   45
  9  ω      3.00  48.00   1.00    3.00    --   48.87 -35.00 112.00   45
 10  ω    -37.00 -11.00   1.00   12.00    --  -88.36  45.00  60.00   26
 11  ω    -55.00 -13.00   1.00   12.00    --  -88.36  61.00   0.00   42
 12  ω    -37.00  -9.00   1.00   12.00    --  -88.36  45.00  90.00   28
 13  ω    -35.00 -10.00   1.00   12.00    --  -88.36  45.00-120.00   25
 14  ω    -37.00 -11.00   1.00   12.00    --  -88.36  45.00 -90.00   26
 15  ω    -37.00 -12.00   1.00   12.00    --  -88.36  45.00-150.00   25
 16  ω     35.00  83.00   1.00   12.00    --  107.71 -61.00-180.00   48
 17  ω     40.00  81.00   1.00   12.00    --  107.71 -61.00   0.00   41
 18  ω     98.00 127.00   1.00   12.00    --  107.71 -77.00 -90.00   29
 19  ω     59.00  86.00   1.00   12.00    --  107.71 -77.00 -90.00   27
 20  ω     32.00  58.00   1.00   12.00    --  107.71 -45.00 -90.00   26
 21  ω     32.00  58.00   1.00   12.00    --  107.71 -45.00 120.00   26
 22  ω     78.00 127.00   1.00   12.00    --  107.71 -77.00-180.00   49
 23  ω     57.00 105.00   1.00   12.00    --  107.71 -95.00 150.00   48
 24  ω     33.00  58.00   1.00   12.00    --  107.71 -61.00 -30.00   25
 25  ω     28.00  61.00   1.00   12.00    --  107.71 -45.00  90.00   33
 26  ω     45.00  79.00   1.00   12.00    --  107.71 -61.00 150.00   34
 27  ω     54.00  81.00   1.00   12.00    --  107.71 -61.00-150.00   27
 28  ω     32.00  85.00   1.00   12.00    --  107.71 -61.00 -90.00   53
 29  ω     29.00  56.00   1.00   12.00    --  107.71 -45.00 -60.00   27
 30  ω     62.00  88.00   1.00    3.00    --   48.87  77.00  90.00   26
 31  ω     -3.00  22.00   1.00    3.00    --  -47.93  19.00  60.00   25
 32  ω    -61.00 -36.00   1.00   12.00    --  -88.36  61.00-120.00   25
 33  ω    -37.00 -12.00   1.00   12.00    --  -88.36  45.00  30.00   25
 34  ω    -35.00 -10.00   1.00   12.00    --  -88.36  45.00 -30.00   25
 35  ω     95.00 159.00   1.00   12.00    --  107.71  30.00-180.00   64
 36  ω     57.00  84.00   1.00   12.00    --  107.71 -61.00 -60.00   27
 37  ω     67.00  94.00   1.00   12.00    --  107.71 -95.00   0.00   27
 38  ω     28.00  53.00   1.00   12.00    --  107.71 -45.00   0.00   25
 39  ω     36.00  84.00   1.00   12.00    --  107.71 -61.00-150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001660000
_diffrn_orient_matrix_UB_12      0.0905498000
_diffrn_orient_matrix_UB_13      0.1150348000
_diffrn_orient_matrix_UB_21      0.1690770000
_diffrn_orient_matrix_UB_22      0.0159769000
_diffrn_orient_matrix_UB_23      0.0452131000
_diffrn_orient_matrix_UB_31      -0.0145380000
_diffrn_orient_matrix_UB_32      0.1872043000
_diffrn_orient_matrix_UB_33      -0.0595266000
_diffrn_oxdiff_digest_frames     
;
019f7ff9b767f0dde43da29361dc718508013901bdf
;
_diffrn_oxdiff_digest_hkl        
;
0186cc437959e5cadcf4728a25257853718930
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2900
_reflns_number_total             3052
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1022P)²+0.1125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1420
_refine_special_details          'Refined as a 2-component perfect twin.,Twin'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.25568(12) 0.25649(16) 0.57742(11) 0.0221(3) Uani 1 1 d . . . . .
C2 C 0.33392(14) 0.33253(19) 0.68290(11) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.2837 0.3596 0.7351 0.026 Uiso 1 1 calc R . . . .
C3 C 0.48246(14) 0.37426(17) 0.72097(11) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.5307 0.4289 0.7966 0.022 Uiso 1 1 calc R . . . .
C4 C 0.56150(13) 0.33540(16) 0.64711(11) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.48053(14) 0.25852(17) 0.53652(12) 0.0192(3) Uani 1 1 d . . . . .
H5 H 0.5271 0.2306 0.4819 0.023 Uiso 1 1 calc R . . . .
C6 C 0.33139(14) 0.22330(18) 0.50707(12) 0.0215(3) Uani 1 1 d . . . . .
H6 H 0.2793 0.1717 0.4311 0.026 Uiso 1 1 calc R . . . .
N7 N 0.71084(11) 0.37631(14) 0.68195(9) 0.0166(3) Uani 1 1 d . . . . .
C8 C 0.80443(13) 0.34299(18) 0.80675(11) 0.0183(3) Uani 1 1 d . . . . .
H8A H 0.8201 0.2112 0.8204 0.022 Uiso 1 1 calc R . . . .
H8B H 0.7548 0.3887 0.8595 0.022 Uiso 1 1 calc R . . . .
C9 C 0.95180(13) 0.43709(18) 0.83662(11) 0.0195(3) Uani 1 1 d . . . . .
H9A H 0.9363 0.5697 0.8303 0.023 Uiso 1 1 calc R . . . .
H9B H 1.0154 0.4087 0.9198 0.023 Uiso 1 1 calc R . . . .
O10 O 1.02430(9) 0.38191(12) 0.75867(8) 0.0197(3) Uani 1 1 d . . . . .
C11 C 0.93412(13) 0.42545(18) 0.63875(11) 0.0195(3) Uani 1 1 d . . . . .
H11A H 0.9854 0.3889 0.5851 0.023 Uiso 1 1 calc R . . . .
H11B H 0.9187 0.5581 0.6314 0.023 Uiso 1 1 calc R . . . .
C12 C 0.78522(13) 0.33088(18) 0.60032(11) 0.0182(3) Uani 1 1 d . . . . .
H12A H 0.7235 0.3691 0.5186 0.022 Uiso 1 1 calc R . . . .
H12B H 0.7994 0.1982 0.5999 0.022 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3439(17) . ?
N1 C6 1.3368(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3850(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.4059(17) . ?
C4 C5 1.3981(18) . ?
C4 N7 1.3935(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3900(18) . ?
C6 H6 0.9500 . ?
N7 C8 1.4678(15) . ?
N7 C12 1.4610(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5167(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 O10 1.4282(15) . ?
O10 C11 1.4277(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5230(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 115.10(11) . . ?
N1 C2 H2 117.7 . . ?
N1 C2 C3 124.67(12) . . ?
C3 C2 H2 117.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.67(12) . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 116.04(11) . . ?
N7 C4 C3 121.37(11) . . ?
N7 C4 C5 122.57(11) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.48(12) . . ?
C6 C5 H5 120.3 . . ?
N1 C6 C5 125.02(12) . . ?
N1 C6 H6 117.5 . . ?
C5 C6 H6 117.5 . . ?
C4 N7 C8 117.47(10) . . ?
C4 N7 C12 118.02(10) . . ?
C12 N7 C8 112.19(10) . . ?
N7 C8 H8A 109.6 . . ?
N7 C8 H8B 109.6 . . ?
N7 C8 C9 110.22(10) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
O10 C9 C8 111.60(10) . . ?
O10 C9 H9A 109.3 . . ?
O10 C9 H9B 109.3 . . ?
C11 O10 C9 109.49(9) . . ?
O10 C11 H11A 109.3 . . ?
O10 C11 H11B 109.3 . . ?
O10 C11 C12 111.70(10) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
N7 C12 C11 110.10(10) . . ?
N7 C12 H12A 109.6 . . ?
N7 C12 H12B 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.526
_oxdiff_exptl_absorpt_empirical_full_min 0.514
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4885 5233 2188 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.5115 5227 2188 nmt 0.9999 0.0000 0.5923 0.0001 -1.0000 0.0002 -0.0000
0.0002 -1.0000

_twin_special_details            
;
Component 2 rotated by 179.9925° 
around [1.00 0.00 -0.00] (reciprocal) or [0.96 -0.00 0.28] (direct)
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3b
_database_code_depnum_ccdc_archive 'CCDC 2225070'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2023-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.8(C22 H24 I N3 O4), 0.2(C22 H22 I N3 O5)'
_chemical_formula_sum            'C22 H23.6 I N3 O4.2'
_chemical_formula_weight         524.14
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.8221(2)
_cell_length_b                   8.3335(2)
_cell_length_c                   16.8477(3)
_cell_angle_alpha                88.532(2)
_cell_angle_beta                 83.279(2)
_cell_angle_gamma                84.899(2)
_cell_volume                     1086.23(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16105
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4210
_cell_measurement_theta_min      2.6130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    11.874
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.206
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             526
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -11 0.0386
0 0 11 0.0166
-1 5 -5 0.0852
0 -5 3 0.0921
3 -4 1 0.0659
-5 -1 -5 0.0768
5 1 -1 0.0983
1 5 4 0.0997
-4 -2 -5 0.0816
4 1 8 0.0777
3 4 -4 0.1049

_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.055
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0020 -0.2816 -10.8530 -0.0766 0.9722 -0.2212
-0.0020 0.2816 10.8530 0.0766 -0.9722 0.2212
-0.7311 4.6915 -4.8755 0.8788 0.4770 -0.0102
0.1855 -5.1663 2.8205 -0.9558 -0.2829 0.0799
3.2469 -3.8347 0.6451 -0.8014 -0.1491 -0.5792
-4.6900 -1.2098 -5.0699 -0.1016 0.5529 0.8270
4.9318 0.7627 -1.2599 -0.0023 0.0074 -1.0000
1.0007 4.9968 3.9936 0.9059 -0.3556 -0.1696
-3.9964 -1.9990 -4.9914 -0.2674 0.5265 0.7017
3.9955 0.9999 7.9913 0.0892 -0.8006 -0.6285
2.9994 3.9971 -4.0062 0.6457 0.3128 -0.7147

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19075
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.488
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1947
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  33.00   1.00    1.00    --   42.00  82.00 -13.85   25
  2  ω   -116.00 -66.00   1.00    1.00    --  -42.17 -37.00   0.00   50
  3  ω    -60.00 -24.00   1.00    1.00    --  -42.17 -37.00   0.00   36
  4  ω     10.00  35.00   1.00    1.00    --   42.17  75.00-156.67   25
  5  ω     68.00 110.00   1.00    1.00    --   42.17  57.00  90.00   42
  6  ω     28.00  94.00   1.00    1.00    --   42.17-125.00 -90.00   66
  7  ω     42.00  91.00   1.00    1.00    --   42.17-125.00  60.00   49
  8  ω     14.00  43.00   1.00    1.00    --   42.17  57.00  90.00   29
  9  ω    -29.00  82.00   1.00    1.00    --   42.17 -19.00 -30.00  111
 10  ω     15.00  41.00   1.00    1.00    --   46.00  76.00 -62.66   26
 11  ω     16.00  42.00   1.00    1.00    --   50.00  81.00  52.31   26
 12  ω     16.00  41.00   1.00    1.00    --   50.00  82.00-158.17   25
 13  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 107.83   25
 14  ω     35.00  61.00   1.00    1.00    --   62.00  58.00  81.60   26
 15  ω     30.00  64.00   1.00    1.00    --   62.00  74.00  16.04   34
 16  ω     98.00 134.00   1.00    1.00    --   62.00  74.00  16.04   36
 17  ω     35.00  61.00   1.00    1.00    --   66.00  72.00-156.31   26
 18  ω     94.00 141.00   1.00    1.00    --   66.00  74.00  91.80   47
 19  ω     36.00  62.00   1.00    1.00    --   66.00  74.00  91.80   26
 20  ω    120.00 145.00   1.00    1.00    --   70.00  74.00 -57.23   25
 21  ω     38.00  73.00   1.00    1.00    --   70.00  74.00 -57.23   35
 22  ω     87.00 145.00   1.00    1.00    --   70.00  74.00 -83.33   58
 23  ω     39.00  67.00   1.00    1.00    --   70.00  74.00 -83.33   28
 24  ω     40.00  76.00   1.00    1.00    --   70.00  72.00 -32.41   36
 25  ω     38.00  68.00   1.00    1.00    --   70.00  73.00-129.24   30
 26  ω    110.00 136.00   1.00    1.00    --   74.00  73.00 113.52   26
 27  ω     43.00  68.00   1.00    1.00    --   74.00  73.00 113.52   25
 28  ω     42.00  79.00   1.00    1.00    --   74.00  73.00 136.73   37
 29  ω     68.00 101.00   1.00    1.00    --   98.00  65.00 -57.54   33
 30  ω    149.00 174.00   1.00    1.00    --  102.00  60.00-109.22   25
 31  ω     73.00 101.00   1.00    1.00    --  102.00  60.00-109.22   28
 32  ω     88.00 116.00   1.00    1.00    --  112.00  45.00   0.00   28
 33  ω     84.00 110.00   1.00    1.00    --  112.00  61.00  30.00   26
 34  ω     37.00  99.00   1.00    1.00    --  112.00-111.00 -60.00   62
 35  ω     88.00 115.00   1.00    1.00    --  112.00  45.00-180.00   27
 36  ω    135.00 178.00   1.00    1.00    --  112.00  61.00 -30.00   43
 37  ω     83.00 109.00   1.00    1.00    --  112.00  61.00 -30.00   26
 38  ω    124.00 153.00   1.00    1.00    --  112.00  61.00 120.00   29
 39  ω     30.00 107.00   1.00    1.00    --  112.00 -94.00   0.00   77
 40  ω     83.00 119.00   1.00    1.00    --  112.00  61.00 120.00   36
 41  ω    121.00 171.00   1.00    1.00    --  112.00  61.00 -60.00   50
 42  ω     86.00 118.00   1.00    1.00    --  112.00  61.00 -60.00   32
 43  ω     34.00 105.00   1.00    1.00    --  112.00 -94.00  90.00   71
 44  ω     83.00 176.00   1.00    1.00    --  112.00  61.00-180.00   93
 45  ω     41.00 107.00   1.00    1.00    --  112.00-111.00 -30.00   66
 46  ω    115.00 166.00   1.00    1.00    --  112.00  61.00-120.00   51
 47  ω     84.00 112.00   1.00    1.00    --  112.00  61.00-120.00   28
 48  ω     31.00  89.00   1.00    1.00    --  112.00 -94.00-120.00   58
 49  ω    129.00 177.00   1.00    1.00    --  112.00  64.00 140.99   48
 50  ω     44.00 109.00   1.00    1.00    --  112.00-111.00-150.00   65
 51  ω     83.00 161.00   1.00    1.00    --  112.00  61.00-150.00   78
 52  ω     83.00 157.00   1.00    1.00    --  112.00  61.00  60.00   74
 53  ω     82.00 111.00   1.00    1.00    --  112.00  64.00 140.99   29
 54  ω     84.00 178.00   1.00    1.00    --  112.00  61.00  90.00   94
 55  ω    131.00 157.00   1.00    1.00    --  112.00  61.00   0.00   26
 56  ω     83.00 178.00   1.00    1.00    --  112.00  59.00  19.44   95
 57  ω     83.00 118.00   1.00    1.00    --  112.00  61.00   0.00   35
 58  ω    113.00 139.00   1.00    1.00    --  112.00 -61.00   0.00   26
 59  ω     41.00  91.00   1.00    1.00    --  112.00 -61.00   0.00   50
 60  ω     83.00 163.00   1.00    1.00    --  112.00  61.00 -90.00   80
 61  ω    127.00 152.00   1.00    1.00    --  112.00  45.00  60.00   25
 62  ω     38.00  78.00   1.00    1.00    --  112.00 -94.00 150.00   40
 63  ω     56.00 109.00   1.00    1.00    --  112.00-111.00-120.00   53
 64  ω     88.00 115.00   1.00    1.00    --  112.00  45.00  60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0285336000
_diffrn_orient_matrix_UB_12      0.1852126000
_diffrn_orient_matrix_UB_13      0.0022478000
_diffrn_orient_matrix_UB_21      -0.0221909000
_diffrn_orient_matrix_UB_22      0.0049870000
_diffrn_orient_matrix_UB_23      -0.0897143000
_diffrn_orient_matrix_UB_31      -0.1957503000
_diffrn_orient_matrix_UB_32      -0.0112298000
_diffrn_orient_matrix_UB_33      0.0206353000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                8132
_reflns_number_total             8298
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 3699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         8298
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.6396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0614
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
3. Others
 Fixed Sof: O12(0.2) O62(0.2) H11A(0.8) H11B(0.8) H61A(0.8) H61B(0.8)
4.a Ternary CH refined with riding coordinates:
 C24(H24), C36(H36), C74(H74), C86(H86)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C58(H58A,H58B),
 C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C28(H28), C29(H29), C30(H30), C31(H31),
 C52(H52), C53(H53), C55(H55), C56(H56), C78(H78), C79(H79), C80(H80), C81(H81)
4.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C87(H87A,H87B,H87C), C88(H88A,H88B,
 H88C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.34879(2) 0.41383(2) 0.62276(2) 0.02749(9) Uani 1 1 d . . . . .
I2 I 0.66647(3) 0.53557(2) 0.36981(2) 0.03001(10) Uani 1 1 d . . . . .
O12 O -0.413(4) 0.105(4) 0.4866(15) 0.044(7) Uani 0.2 1 d . . P A 2
O21 O 0.5286(8) 0.5093(6) 0.6979(3) 0.0359(11) Uani 1 1 d . . . . .
O23 O 0.6335(7) 0.2612(5) 0.7274(3) 0.0472(12) Uani 1 1 d . . . . .
O34 O 0.4038(5) 0.4678(5) 0.8963(3) 0.0402(9) Uani 1 1 d . . . . .
O35 O 0.7643(6) 0.8309(6) 0.7821(3) 0.0469(12) Uani 1 1 d . . . . .
O62 O 1.406(3) 0.846(3) 0.5123(16) 0.037(6) Uani 0.2 1 d . . P B 2
O71 O 0.5197(8) 0.4426(7) 0.2770(3) 0.0470(15) Uani 1 1 d . . . . .
O73 O 0.3238(7) 0.6505(8) 0.2944(3) 0.0629(18) Uani 1 1 d . . . . .
O84 O 0.2626(6) 0.1612(6) 0.2349(2) 0.0407(10) Uani 1 1 d . . . . .
O85 O 0.6096(5) 0.4423(5) 0.0552(2) 0.0396(9) Uani 1 1 d . . . . .
N1 N 0.1610(8) 0.3264(8) 0.5463(3) 0.0272(12) Uani 1 1 d . . . . .
N7 N -0.1567(7) 0.1118(7) 0.4075(3) 0.0259(11) Uani 1 1 d . U . . .
N25 N 0.6139(8) 0.6184(7) 0.8338(3) 0.0271(12) Uani 1 1 d . . . . .
N51 N 0.8384(8) 0.6275(7) 0.4522(4) 0.0262(12) Uani 1 1 d . . . . .
N57 N 1.1545(7) 0.8420(6) 0.5923(3) 0.0248(11) Uani 1 1 d . . . . .
N75 N 0.4041(8) 0.3380(7) 0.1479(3) 0.0291(12) Uani 1 1 d . . . . .
C2 C 0.2059(9) 0.3039(8) 0.4675(4) 0.0290(13) Uani 1 1 d . . . . .
H2 H 0.3128 0.3390 0.4438 0.035 Uiso 1 1 calc R . . . .
C3 C 0.1063(10) 0.2338(9) 0.4203(4) 0.0281(14) Uani 1 1 d . . . . .
H3 H 0.1442 0.2196 0.3651 0.034 Uiso 1 1 calc R . . . .
C4 C -0.0562(8) 0.1811(7) 0.4538(4) 0.0231(12) Uani 1 1 d . . . . .
C5 C -0.1033(9) 0.2081(8) 0.5358(3) 0.0263(13) Uani 1 1 d . . . . .
H5 H -0.2106 0.1773 0.5612 0.032 Uiso 1 1 calc R . . . .
C6 C 0.0072(9) 0.2792(8) 0.5787(3) 0.0267(13) Uani 1 1 d . . . . .
H6 H -0.0263 0.2960 0.6341 0.032 Uiso 1 1 calc R . . . .
C8 C -0.1071(9) 0.0839(9) 0.3217(4) 0.0312(14) Uani 1 1 d . U . . .
H8A H 0.0068 0.0212 0.3123 0.037 Uiso 1 1 calc R . . . .
H8B H -0.1024 0.1870 0.2914 0.037 Uiso 1 1 calc R . . . .
C9 C -0.2488(11) -0.0108(10) 0.2981(5) 0.0381(16) Uani 1 1 d . U . . .
H9A H -0.2182 -0.1281 0.3033 0.046 Uiso 1 1 calc R . . . .
H9B H -0.2707 0.0149 0.2422 0.046 Uiso 1 1 calc R . . . .
C10 C -0.4066(10) 0.0433(10) 0.3567(5) 0.0393(16) Uani 1 1 d . U . . .
H10A H -0.4676 0.1433 0.3373 0.047 Uiso 1 1 calc R . . . .
H10B H -0.4882 -0.0415 0.3643 0.047 Uiso 1 1 calc R . . . .
C11 C -0.3316(10) 0.0724(9) 0.4342(5) 0.0335(15) Uani 1 1 d . U . . .
H11A H -0.3986 0.1626 0.4640 0.040 Uiso 0.8 1 calc R . P A 1
H11B H -0.3310 -0.0254 0.4688 0.040 Uiso 0.8 1 calc R . P A 1
C22 C 0.6186(10) 0.4060(8) 0.7347(4) 0.0280(13) Uani 1 1 d . . . . .
C24 C 0.7271(8) 0.4873(7) 0.7927(3) 0.0296(12) Uani 1 1 d . . . . .
H24 H 0.8193 0.5402 0.7581 0.035 Uiso 1 1 calc R . . . .
C26 C 0.4608(8) 0.5970(8) 0.8819(4) 0.0309(13) Uani 1 1 d . . . . .
C27 C 0.3895(9) 0.7596(8) 0.9086(4) 0.0294(13) Uani 1 1 d . . . . .
C28 C 0.2442(8) 0.8088(8) 0.9595(4) 0.0380(13) Uani 1 1 d . . . . .
H28 H 0.1687 0.7340 0.9839 0.046 Uiso 1 1 calc R . . . .
C29 C 0.2131(9) 0.9742(8) 0.9734(4) 0.0419(14) Uani 1 1 d . . . . .
H29 H 0.1163 1.0117 1.0096 0.050 Uiso 1 1 calc R . . . .
C30 C 0.3181(9) 1.0838(8) 0.9365(4) 0.0392(15) Uani 1 1 d . . . . .
H30 H 0.2914 1.1952 0.9471 0.047 Uiso 1 1 calc R . . . .
C31 C 0.4636(9) 1.0349(8) 0.8837(4) 0.0351(13) Uani 1 1 d . . . . .
H31 H 0.5351 1.1108 0.8571 0.042 Uiso 1 1 calc R . . . .
C32 C 0.4987(9) 0.8712(8) 0.8718(4) 0.0291(13) Uani 1 1 d . . . . .
C33 C 0.6420(10) 0.7814(8) 0.8235(4) 0.0330(15) Uani 1 1 d . . . . .
C36 C 0.8191(7) 0.3798(6) 0.8520(3) 0.0319(10) Uani 1 1 d . . . . .
H36 H 0.7304 0.3237 0.8873 0.038 Uiso 1 1 calc R . . . .
C37 C 0.9495(11) 0.2526(11) 0.8109(5) 0.0439(19) Uani 1 1 d . . . . .
H37A H 1.0361 0.3055 0.7751 0.066 Uiso 1 1 calc GR . . . .
H37B H 0.8896 0.1821 0.7798 0.066 Uiso 1 1 calc GR . . . .
H37C H 1.0067 0.1883 0.8513 0.066 Uiso 1 1 calc GR . . . .
C38 C 0.9123(9) 0.4832(9) 0.9045(4) 0.0414(15) Uani 1 1 d . . . . .
H38A H 0.9784 0.4129 0.9396 0.062 Uiso 1 1 calc GR . . . .
H38B H 0.8270 0.5547 0.9369 0.062 Uiso 1 1 calc GR . . . .
H38C H 0.9910 0.5478 0.8704 0.062 Uiso 1 1 calc GR . . . .
C52 C 0.9939(9) 0.6719(8) 0.4212(4) 0.0271(13) Uani 1 1 d . . . . .
H52 H 1.0301 0.6528 0.3662 0.032 Uiso 1 1 calc R . . . .
C53 C 1.1022(9) 0.7425(8) 0.4644(4) 0.0260(13) Uani 1 1 d . . . . .
H53 H 1.2109 0.7712 0.4397 0.031 Uiso 1 1 calc R . . . .
C54 C 1.0512(8) 0.7730(7) 0.5467(3) 0.0227(12) Uani 1 1 d . . . . .
C55 C 0.8886(9) 0.7273(8) 0.5786(4) 0.0264(14) Uani 1 1 d . . . . .
H55 H 0.8481 0.7461 0.6332 0.032 Uiso 1 1 calc R . . . .
C56 C 0.7871(9) 0.6547(8) 0.5303(4) 0.0276(13) Uani 1 1 d . . . . .
H56 H 0.6779 0.6231 0.5530 0.033 Uiso 1 1 calc R . . . .
C58 C 1.1053(10) 0.8725(8) 0.6776(3) 0.0307(14) Uani 1 1 d . . . . .
H58A H 1.1008 0.7704 0.7089 0.037 Uiso 1 1 calc R . . . .
H58B H 0.9916 0.9356 0.6869 0.037 Uiso 1 1 calc R . . . .
C59 C 1.2499(11) 0.9688(9) 0.6995(5) 0.0358(15) Uani 1 1 d . . . . .
H59A H 1.2213 1.0858 0.6915 0.043 Uiso 1 1 calc R . . . .
H59B H 1.2707 0.9481 0.7559 0.043 Uiso 1 1 calc R . . . .
C60 C 1.4062(9) 0.9083(9) 0.6428(4) 0.0346(15) Uani 1 1 d . . . . .
H60A H 1.4626 0.8070 0.6632 0.042 Uiso 1 1 calc R . . . .
H60B H 1.4916 0.9897 0.6346 0.042 Uiso 1 1 calc R . . . .
C61 C 1.3290(9) 0.8802(9) 0.5655(4) 0.0321(14) Uani 1 1 d . . . . .
H61A H 1.3288 0.9782 0.5310 0.038 Uiso 0.8 1 calc R . P B 1
H61B H 1.3949 0.7898 0.5354 0.038 Uiso 0.8 1 calc R . P B 1
C72 C 0.3930(9) 0.5319(8) 0.2603(4) 0.0267(13) Uani 1 1 d . . . . .
C74 C 0.3214(8) 0.4908(7) 0.1786(3) 0.0296(12) Uani 1 1 d . . . . .
H74 H 0.3607 0.5750 0.1389 0.036 Uiso 1 1 calc R . . . .
C76 C 0.3711(9) 0.1857(8) 0.1802(4) 0.0284(13) Uani 1 1 d . . . . .
C77 C 0.4963(9) 0.0689(8) 0.1332(4) 0.0306(14) Uani 1 1 d . . . . .
C78 C 0.5130(9) -0.0982(8) 0.1378(4) 0.0396(14) Uani 1 1 d . . . . .
H78 H 0.4394 -0.1566 0.1745 0.047 Uiso 1 1 calc R . . . .
C79 C 0.6439(9) -0.1755(7) 0.0855(4) 0.0442(15) Uani 1 1 d . . . . .
H79 H 0.6601 -0.2898 0.0866 0.053 Uiso 1 1 calc R . . . .
C80 C 0.7495(9) -0.0915(9) 0.0327(4) 0.0411(15) Uani 1 1 d . . . . .
H80 H 0.8356 -0.1491 -0.0027 0.049 Uiso 1 1 calc R . . . .
C81 C 0.7344(8) 0.0762(8) 0.0292(4) 0.0370(13) Uani 1 1 d . . . . .
H81 H 0.8103 0.1345 -0.0064 0.044 Uiso 1 1 calc R . . . .
C82 C 0.6026(9) 0.1539(8) 0.0805(4) 0.0293(14) Uani 1 1 d . . . . .
C83 C 0.5473(8) 0.3289(8) 0.0896(3) 0.0305(13) Uani 1 1 d . . . . .
C86 C 0.1231(7) 0.5037(7) 0.1831(3) 0.0344(11) Uani 1 1 d . . . . .
H86 H 0.0763 0.4527 0.2346 0.041 Uiso 1 1 calc R . . . .
C87 C 0.0511(12) 0.6817(10) 0.1824(5) 0.0419(19) Uani 1 1 d . . . . .
H87A H 0.0857 0.7361 0.2281 0.063 Uiso 1 1 calc GR . . . .
H87B H -0.0752 0.6882 0.1860 0.063 Uiso 1 1 calc GR . . . .
H87C H 0.0971 0.7340 0.1327 0.063 Uiso 1 1 calc GR . . . .
C88 C 0.0613(10) 0.4166(10) 0.1142(4) 0.0492(17) Uani 1 1 d . . . . .
H88A H 0.1241 0.4497 0.0635 0.074 Uiso 1 1 calc GR . . . .
H88B H -0.0628 0.4445 0.1131 0.074 Uiso 1 1 calc GR . . . .
H88C H 0.0831 0.3000 0.1218 0.074 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O21 2.209(5) . ?
I1 N1 2.243(6) . ?
I2 O71 2.237(5) . ?
I2 N51 2.235(6) . ?
O12 C11 1.05(3) . ?
O21 C22 1.260(9) . ?
O23 C22 1.210(8) . ?
O34 C26 1.210(7) . ?
O35 C33 1.212(8) . ?
O62 C61 1.05(3) . ?
O71 C72 1.240(9) . ?
O73 C72 1.209(8) . ?
O84 C76 1.204(8) . ?
O85 C83 1.205(7) . ?
N1 C2 1.347(9) . ?
N1 C6 1.349(10) . ?
N7 C4 1.343(9) . ?
N7 C8 1.471(8) . ?
N7 C11 1.453(9) . ?
N25 C24 1.476(8) . ?
N25 C26 1.388(9) . ?
N25 C33 1.398(9) . ?
N51 C52 1.346(9) . ?
N51 C56 1.350(8) . ?
N57 C54 1.350(8) . ?
N57 C58 1.467(7) . ?
N57 C61 1.448(9) . ?
N75 C74 1.455(8) . ?
N75 C76 1.401(9) . ?
N75 C83 1.398(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.352(10) . ?
C3 H3 0.9500 . ?
C3 C4 1.430(10) . ?
C4 C5 1.407(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.371(9) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.512(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.529(12) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.526(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C22 C24 1.570(9) . ?
C24 H24 1.0000 . ?
C24 C36 1.525(7) . ?
C26 C27 1.479(9) . ?
C27 C28 1.379(9) . ?
C27 C32 1.402(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.399(9) . ?
C29 H29 0.9500 . ?
C29 C30 1.371(10) . ?
C30 H30 0.9500 . ?
C30 C31 1.397(10) . ?
C31 H31 0.9500 . ?
C31 C32 1.383(9) . ?
C32 C33 1.466(10) . ?
C36 H36 1.0000 . ?
C36 C37 1.524(9) . ?
C36 C38 1.535(8) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C52 H52 0.9500 . ?
C52 C53 1.358(9) . ?
C53 H53 0.9500 . ?
C53 C54 1.421(8) . ?
C54 C55 1.402(10) . ?
C55 H55 0.9500 . ?
C55 C56 1.385(10) . ?
C56 H56 0.9500 . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C58 C59 1.528(10) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C59 C60 1.517(11) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C60 C61 1.531(10) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C72 C74 1.602(9) . ?
C74 H74 1.0000 . ?
C74 C86 1.538(8) . ?
C76 C77 1.490(9) . ?
C77 C78 1.388(9) . ?
C77 C82 1.372(9) . ?
C78 H78 0.9500 . ?
C78 C79 1.393(10) . ?
C79 H79 0.9500 . ?
C79 C80 1.364(10) . ?
C80 H80 0.9500 . ?
C80 C81 1.393(9) . ?
C81 H81 0.9500 . ?
C81 C82 1.389(9) . ?
C82 C83 1.491(9) . ?
C86 H86 1.0000 . ?
C86 C87 1.539(10) . ?
C86 C88 1.532(8) . ?
C87 H87A 0.9800 . ?
C87 H87B 0.9800 . ?
C87 H87C 0.9800 . ?
C88 H88A 0.9800 . ?
C88 H88B 0.9800 . ?
C88 H88C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O21 I1 N1 177.8(2) . . ?
N51 I2 O71 173.7(3) . . ?
C22 O21 I1 116.1(4) . . ?
C72 O71 I2 115.4(5) . . ?
C2 N1 I1 120.6(5) . . ?
C2 N1 C6 117.8(6) . . ?
C6 N1 I1 121.2(4) . . ?
C4 N7 C8 123.0(5) . . ?
C4 N7 C11 124.0(5) . . ?
C11 N7 C8 112.7(5) . . ?
C26 N25 C24 124.6(5) . . ?
C26 N25 C33 111.8(6) . . ?
C33 N25 C24 123.4(6) . . ?
C52 N51 I2 118.7(4) . . ?
C52 N51 C56 118.2(6) . . ?
C56 N51 I2 122.9(5) . . ?
C54 N57 C58 122.5(5) . . ?
C54 N57 C61 124.7(5) . . ?
C61 N57 C58 112.5(5) . . ?
C76 N75 C74 125.4(5) . . ?
C83 N75 C74 122.3(6) . . ?
C83 N75 C76 111.6(6) . . ?
N1 C2 H2 118.4 . . ?
N1 C2 C3 123.2(7) . . ?
C3 C2 H2 118.4 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(6) . . ?
C4 C3 H3 120.1 . . ?
N7 C4 C3 120.5(6) . . ?
N7 C4 C5 123.1(6) . . ?
C5 C4 C3 116.4(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
N1 C6 C5 123.3(6) . . ?
N1 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
N7 C8 H8A 111.0 . . ?
N7 C8 H8B 111.0 . . ?
N7 C8 C9 103.7(6) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C8 C9 C10 104.2(6) . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C11 C10 C9 104.2(6) . . ?
C11 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
O12 C11 N7 130.0(18) . . ?
O12 C11 C10 120.9(18) . . ?
N7 C11 C10 103.8(6) . . ?
N7 C11 H11A 111.0 . . ?
N7 C11 H11B 111.0 . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
O21 C22 C24 111.6(5) . . ?
O23 C22 O21 128.2(7) . . ?
O23 C22 C24 120.1(6) . . ?
N25 C24 C22 107.6(5) . . ?
N25 C24 H24 106.3 . . ?
N25 C24 C36 111.3(5) . . ?
C22 C24 H24 106.3 . . ?
C36 C24 C22 118.2(5) . . ?
C36 C24 H24 106.3 . . ?
O34 C26 N25 124.2(6) . . ?
O34 C26 C27 129.8(6) . . ?
N25 C26 C27 106.0(5) . . ?
C28 C27 C26 131.0(6) . . ?
C28 C27 C32 121.2(6) . . ?
C32 C27 C26 107.9(6) . . ?
C27 C28 H28 121.5 . . ?
C27 C28 C29 116.9(6) . . ?
C29 C28 H28 121.5 . . ?
C28 C29 H29 119.0 . . ?
C30 C29 C28 122.0(6) . . ?
C30 C29 H29 119.0 . . ?
C29 C30 H30 119.3 . . ?
C29 C30 C31 121.3(6) . . ?
C31 C30 H30 119.3 . . ?
C30 C31 H31 121.5 . . ?
C32 C31 C30 117.0(6) . . ?
C32 C31 H31 121.5 . . ?
C27 C32 C33 107.9(6) . . ?
C31 C32 C27 121.5(6) . . ?
C31 C32 C33 130.5(6) . . ?
O35 C33 N25 124.2(7) . . ?
O35 C33 C32 129.5(7) . . ?
N25 C33 C32 106.3(6) . . ?
C24 C36 H36 108.4 . . ?
C24 C36 C38 109.8(5) . . ?
C37 C36 C24 112.6(5) . . ?
C37 C36 H36 108.4 . . ?
C37 C36 C38 109.1(6) . . ?
C38 C36 H36 108.4 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N51 C52 H52 118.2 . . ?
N51 C52 C53 123.6(6) . . ?
C53 C52 H52 118.2 . . ?
C52 C53 H53 120.3 . . ?
C52 C53 C54 119.4(6) . . ?
C54 C53 H53 120.3 . . ?
N57 C54 C53 121.7(6) . . ?
N57 C54 C55 121.5(5) . . ?
C55 C54 C53 116.8(6) . . ?
C54 C55 H55 120.0 . . ?
C56 C55 C54 120.0(6) . . ?
C56 C55 H55 120.0 . . ?
N51 C56 C55 122.1(6) . . ?
N51 C56 H56 119.0 . . ?
C55 C56 H56 119.0 . . ?
N57 C58 H58A 111.2 . . ?
N57 C58 H58B 111.2 . . ?
N57 C58 C59 103.0(6) . . ?
H58A C58 H58B 109.1 . . ?
C59 C58 H58A 111.2 . . ?
C59 C58 H58B 111.2 . . ?
C58 C59 H59A 110.9 . . ?
C58 C59 H59B 110.9 . . ?
H59A C59 H59B 109.0 . . ?
C60 C59 C58 104.1(6) . . ?
C60 C59 H59A 110.9 . . ?
C60 C59 H59B 110.9 . . ?
C59 C60 H60A 111.1 . . ?
C59 C60 H60B 111.1 . . ?
C59 C60 C61 103.2(6) . . ?
H60A C60 H60B 109.1 . . ?
C61 C60 H60A 111.1 . . ?
C61 C60 H60B 111.1 . . ?
O62 C61 N57 128.4(16) . . ?
O62 C61 C60 122.2(16) . . ?
N57 C61 C60 104.1(6) . . ?
N57 C61 H61A 110.9 . . ?
N57 C61 H61B 110.9 . . ?
C60 C61 H61A 110.9 . . ?
C60 C61 H61B 110.9 . . ?
H61A C61 H61B 109.0 . . ?
O71 C72 C74 114.9(5) . . ?
O73 C72 O71 129.0(7) . . ?
O73 C72 C74 116.0(6) . . ?
N75 C74 C72 110.3(5) . . ?
N75 C74 H74 106.0 . . ?
N75 C74 C86 113.8(5) . . ?
C72 C74 H74 106.0 . . ?
C86 C74 C72 114.2(5) . . ?
C86 C74 H74 106.0 . . ?
O84 C76 N75 124.9(6) . . ?
O84 C76 C77 129.4(6) . . ?
N75 C76 C77 105.6(5) . . ?
C78 C77 C76 129.4(6) . . ?
C82 C77 C76 108.4(6) . . ?
C82 C77 C78 122.2(6) . . ?
C77 C78 H78 121.9 . . ?
C77 C78 C79 116.2(6) . . ?
C79 C78 H78 121.9 . . ?
C78 C79 H79 119.1 . . ?
C80 C79 C78 121.8(6) . . ?
C80 C79 H79 119.1 . . ?
C79 C80 H80 119.1 . . ?
C79 C80 C81 121.8(6) . . ?
C81 C80 H80 119.1 . . ?
C80 C81 H81 121.7 . . ?
C82 C81 C80 116.6(6) . . ?
C82 C81 H81 121.7 . . ?
C77 C82 C81 121.3(6) . . ?
C77 C82 C83 108.4(6) . . ?
C81 C82 C83 130.2(6) . . ?
O85 C83 N75 125.5(6) . . ?
O85 C83 C82 128.7(6) . . ?
N75 C83 C82 105.7(6) . . ?
C74 C86 H86 108.4 . . ?
C74 C86 C87 110.3(6) . . ?
C87 C86 H86 108.4 . . ?
C88 C86 C74 111.9(5) . . ?
C88 C86 H86 108.4 . . ?
C88 C86 C87 109.4(5) . . ?
C86 C87 H87A 109.5 . . ?
C86 C87 H87B 109.5 . . ?
C86 C87 H87C 109.5 . . ?
H87A C87 H87B 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
C86 C88 H88A 109.5 . . ?
C86 C88 H88B 109.5 . . ?
C86 C88 H88C 109.5 . . ?
H88A C88 H88B 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?


_ins_header                      
;
TITL TIO-118_numabs in P1 
REM P1 (#1 in standard setting)
CELL 1.54184   7.822090   8.333541  16.847662  88.5322  83.2788  84.8994
ZERR    2.00   0.000188   0.000172   0.000336   0.0016   0.0018   0.0018
LATT -1
SFAC C H N O I
UNIT 44.00 48.00 6.00 8.00 2.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.824
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3c
_database_code_depnum_ccdc_archive 'CCDC 2225071'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-12-07 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_PLAT342_TIO-104_2_numabs_ana2 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02069 Ang.  
RESPONSE: All the crystals were 
found to be heavily twinned 
plates, with data collected on 
the best of those tested. The 
data could not be fully 
processed as two twin components 
or accounted for using an 
appropriate twin law, resulting 
in a detrimental effect to the 
bond precision of the light 
atoms in the model. However, 
the identity of the compound 
was clearly established without 
issue.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 I N3 O5'
_chemical_formula_sum            'C22 H24 I N3 O5'
_chemical_formula_weight         537.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   15.4356(3)
_cell_length_b                   7.9667(2)
_cell_length_c                   36.8918(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.429(2)
_cell_angle_gamma                90
_cell_volume                     4446.66(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6778
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.9130
_cell_measurement_theta_min      2.9230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    11.646
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_correction_T_min  0.167
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2160
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -23 0.0084
2 -5 -4 0.1655
-10 0 7 0.0743
10 0 -7 0.0863
0 -5 -3 0.1771
0 5 3 0.1571
0 0 23 0.0094

_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.018
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.2477 0.2680 -23.3085 -0.0783 0.9962 0.0386
2.0146 -5.0032 -3.9843 0.9231 0.1618 -0.3386
-9.9530 0.0525 7.4116 -0.5335 -0.0997 -0.8399
9.9530 -0.0525 -7.4116 0.5335 0.0997 0.8399
0.3485 -5.1301 -3.0238 0.8557 0.1580 -0.4928
-0.3485 5.1301 3.0238 -0.8557 -0.1580 0.4928
0.2477 -0.2680 23.3085 0.0783 -0.9962 -0.0386

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            15985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_min         2.444
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1947
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -10.00   1.00    1.00    --  -41.92 125.00  90.00   52
  2  ω   -114.00 -30.00   1.00    1.00    --  -41.92 -37.00 -60.00   84
  3  ω   -129.00  13.00   1.00    1.00    --  -41.92   0.00  90.00  142
  4  ω    -80.00  -6.00   1.00    1.00    --  -41.92 125.00  30.00   74
  5  ω     86.00 178.00   1.00    5.00    --  112.00  30.00-150.00   92
  6  ω     85.00 177.00   1.00    5.00    --  112.00  61.00  30.00   92
  7  ω     41.00  69.00   1.00    5.00    --  112.00 -61.00 -30.00   28
  8  ω    103.00 177.00   1.00    5.00    --  112.00  77.00  90.00   74
  9  ω     93.00 136.00   1.00    5.00    --  112.00  45.00   0.00   43
 10  ω     83.00 118.00   1.00    5.00    --  112.00  61.00 150.00   35
 11  ω    134.00 173.00   1.00    5.00    --  112.00  61.00 150.00   39
 12  ω    103.00 174.00   1.00    5.00    --  112.00  77.00  60.00   71
 13  ω     36.00 105.00   1.00    5.00    --  112.00-111.00  60.00   69
 14  ω    104.00 177.00   1.00    5.00    --  112.00 111.00 -30.00   73
 15  ω     37.00 123.00   1.00    5.00    --  112.00 -77.00 -90.00   86
 16  ω    120.00 166.00   1.00    5.00    --  112.00  77.00 120.00   46
 17  ω     91.00 137.00   1.00    5.00    --  112.00 -61.00 -30.00   46
 18  ω    153.00 178.00   1.00    5.00    --  112.00  45.00   0.00   25
 19  ω     46.00  89.00   1.00    5.00    --  112.00-111.00 -90.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0534124000
_diffrn_orient_matrix_UB_12      -0.1637078000
_diffrn_orient_matrix_UB_13      0.0009071000
_diffrn_orient_matrix_UB_21      -0.0217369000
_diffrn_orient_matrix_UB_22      -0.0071679000
_diffrn_orient_matrix_UB_23      -0.0425906000
_diffrn_orient_matrix_UB_31      0.0839100000
_diffrn_orient_matrix_UB_32      0.1025603000
_diffrn_orient_matrix_UB_33      -0.0013685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                8281
_reflns_number_total             8930
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.620
_refine_diff_density_min         -1.636
_refine_diff_density_rms         0.184
_refine_ls_abs_structure_details 
;
 Flack x determined using 3400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         8930
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0714
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1114P)²+47.1892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.1958
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O121-C122
 1.3 with sigma of 0.01
 O123-C122
 1.15 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C24) = Uanis(C22)
4. Rigid body (RIGU) restrains
5.a Ternary CH refined with riding coordinates:
 C24(H24), C36(H36), C124(H124), C136(H136)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C108(H10A,H10B),
 C109(H10C,H10D), C111(H11C,H11D), C112(H11E,H11F)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C28(H28), C29(H29), C30(H30), C31(H31),
 C102(H102), C103(H103), C105(H105), C106(H106), C128(H128), C129(H129),
 C130(H130), C131(H131)
5.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C137(H13A,H13B,H13C), C138(H13D,
 H13E,H13F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.61449(5) 0.60032(10) 0.30370(2) 0.0297(2) Uani 1 1 d . . . . .
O10 O 0.9376(6) 0.6073(17) 0.1180(3) 0.037(2) Uani 1 1 d . . . . .
O21 O 0.5602(6) 0.5659(13) 0.3545(3) 0.033(2) Uani 1 1 d . . . . .
O23 O 0.4286(7) 0.4895(17) 0.3203(3) 0.040(3) Uani 1 1 d . . . . .
O34 O 0.5931(9) 0.3829(17) 0.4510(3) 0.047(3) Uani 1 1 d . . . . .
O35 O 0.4183(6) 0.8083(15) 0.3940(3) 0.034(2) Uani 1 1 d . . . . .
N1 N 0.6880(7) 0.6242(18) 0.2573(3) 0.031(3) Uani 1 1 d . . . . .
N7 N 0.8370(7) 0.6228(16) 0.1742(3) 0.027(2) Uani 1 1 d . . . . .
N25 N 0.4934(8) 0.5675(15) 0.4165(3) 0.030(2) Uani 1 1 d . . . . .
C2 C 0.7762(8) 0.591(2) 0.2653(4) 0.033(3) Uani 1 1 d . . . . .
H2 H 0.8028 0.5680 0.2897 0.040 Uiso 1 1 calc R . . . .
C3 C 0.8273(8) 0.591(2) 0.2391(4) 0.032(3) Uani 1 1 d . . . . .
H3 H 0.8872 0.5666 0.2456 0.039 Uiso 1 1 calc R . . . .
C4 C 0.7887(8) 0.629(2) 0.2018(4) 0.030(3) Uani 1 1 d . . . . .
C5 C 0.6984(8) 0.6725(19) 0.1948(4) 0.027(3) Uani 1 1 d . . . . .
H5 H 0.6707 0.7045 0.1711 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6507(8) 0.6680(18) 0.2224(4) 0.028(3) Uani 1 1 d . . . . .
H6 H 0.5910 0.6960 0.2170 0.034 Uiso 1 1 calc R . . . .
C8 C 0.9325(8) 0.604(2) 0.1833(3) 0.029(2) Uani 1 1 d . . . . .
H8A H 0.9489 0.5363 0.2054 0.035 Uiso 1 1 calc R . . . .
H8B H 0.9597 0.7139 0.1884 0.035 Uiso 1 1 calc R . . . .
C9 C 0.9659(10) 0.522(2) 0.1516(4) 0.036(3) Uani 1 1 d . . . . .
H9A H 1.0300 0.5199 0.1573 0.044 Uiso 1 1 calc R . . . .
H9B H 0.9450 0.4073 0.1490 0.044 Uiso 1 1 calc R . . . .
C11 C 0.8435(9) 0.603(2) 0.1084(4) 0.036(3) Uani 1 1 d . . . . .
H11A H 0.8234 0.4877 0.1065 0.043 Uiso 1 1 calc R . . . .
H11B H 0.8241 0.6560 0.0844 0.043 Uiso 1 1 calc R . . . .
C12 C 0.8026(8) 0.695(2) 0.1373(3) 0.030(3) Uani 1 1 d . . . . .
H12A H 0.8171 0.8138 0.1374 0.036 Uiso 1 1 calc R . . . .
H12B H 0.7388 0.6843 0.1313 0.036 Uiso 1 1 calc R . . . .
C22 C 0.4776(8) 0.5098(17) 0.3486(3) 0.0236(17) Uani 1 1 d . . . . .
C24 C 0.4534(7) 0.4532(19) 0.3866(3) 0.0236(17) Uani 1 1 d . . . . .
H24 H 0.4813 0.3435 0.3927 0.028 Uiso 1 1 calc R . . . .
C26 C 0.5634(10) 0.522(2) 0.4453(4) 0.039(3) Uani 1 1 d . . . . .
C27 C 0.5908(10) 0.681(2) 0.4659(4) 0.035(3) Uani 1 1 d . . . . .
C28 C 0.6561(11) 0.711(3) 0.4966(4) 0.043(4) Uani 1 1 d . . . . .
H28 H 0.6916 0.6236 0.5080 0.052 Uiso 1 1 calc R . . . .
C29 C 0.6676(11) 0.872(3) 0.5100(4) 0.047(4) Uani 1 1 d . . . . .
H29 H 0.7101 0.8935 0.5311 0.056 Uiso 1 1 calc R . . . .
C30 C 0.6168(11) 1.003(3) 0.4924(5) 0.044(4) Uani 1 1 d . . . . .
H30 H 0.6267 1.1118 0.5015 0.053 Uiso 1 1 calc R . . . .
C31 C 0.5500(9) 0.974(2) 0.4607(4) 0.037(3) Uani 1 1 d . . . . .
H31 H 0.5156 1.0605 0.4486 0.045 Uiso 1 1 calc R . . . .
C32 C 0.5388(9) 0.813(2) 0.4488(4) 0.030(3) Uani 1 1 d . . . . .
C33 C 0.4761(8) 0.738(2) 0.4166(4) 0.032(3) Uani 1 1 d . . . . .
C36 C 0.3523(9) 0.426(2) 0.3828(4) 0.035(3) Uani 1 1 d . . . . .
H36 H 0.3215 0.5160 0.3673 0.042 Uiso 1 1 calc R . . . .
C37 C 0.3262(11) 0.261(2) 0.3636(5) 0.044(4) Uani 1 1 d . . . . .
H37A H 0.3453 0.2589 0.3404 0.066 Uiso 1 1 calc GR . . . .
H37B H 0.2631 0.2489 0.3594 0.066 Uiso 1 1 calc GR . . . .
H37C H 0.3535 0.1705 0.3789 0.066 Uiso 1 1 calc GR . . . .
C38 C 0.3246(11) 0.433(3) 0.4201(5) 0.053(5) Uani 1 1 d . . . . .
H38A H 0.3574 0.3509 0.4364 0.080 Uiso 1 1 calc GR . . . .
H38B H 0.2626 0.4089 0.4169 0.080 Uiso 1 1 calc GR . . . .
H38C H 0.3363 0.5426 0.4306 0.080 Uiso 1 1 calc GR . . . .
I2 I 0.07736(5) 0.45253(11) 0.29243(2) 0.0323(2) Uani 1 1 d . . . . .
O110 O 0.4327(6) 0.4299(16) 0.1191(3) 0.038(2) Uani 1 1 d . . . . .
O121 O -0.0239(7) 0.4966(15) 0.3283(3) 0.041(2) Uani 1 1 d D U . . .
O123 O 0.0849(6) 0.4737(18) 0.3763(3) 0.047(3) Uani 1 1 d D U . . .
O134 O -0.0871(7) 0.1617(14) 0.4009(3) 0.034(2) Uani 1 1 d . . . . .
O135 O 0.0720(8) 0.6127(16) 0.4557(3) 0.044(3) Uani 1 1 d . . . . .
N101 N 0.1695(8) 0.4104(16) 0.2531(3) 0.032(3) Uani 1 1 d . . . . .
N107 N 0.3289(7) 0.4076(15) 0.1747(3) 0.027(2) Uani 1 1 d . . . . .
N125 N -0.0244(8) 0.4165(16) 0.4218(3) 0.029(2) Uani 1 1 d . . . . .
C102 C 0.2559(9) 0.452(2) 0.2633(4) 0.029(2) Uani 1 1 d . . . . .
H102 H 0.2786 0.4832 0.2877 0.035 Uiso 1 1 calc R . . . .
C103 C 0.3110(9) 0.448(2) 0.2377(4) 0.032(3) Uani 1 1 d . . . . .
H103 H 0.3704 0.4755 0.2452 0.039 Uiso 1 1 calc R . . . .
C104 C 0.2783(8) 0.4031(16) 0.2009(4) 0.025(3) Uani 1 1 d . . . . .
C105 C 0.1897(9) 0.3461(19) 0.1924(4) 0.028(3) Uani 1 1 d . . . . .
H105 H 0.1663 0.3032 0.1691 0.034 Uiso 1 1 calc R . . . .
C106 C 0.1381(8) 0.3546(17) 0.2191(4) 0.029(3) Uani 1 1 d . . . . .
H106 H 0.0794 0.3200 0.2129 0.035 Uiso 1 1 calc R . . . .
C108 C 0.4223(8) 0.450(2) 0.1837(4) 0.031(3) Uani 1 1 d . . . . .
H10A H 0.4568 0.3486 0.1902 0.037 Uiso 1 1 calc R . . . .
H10B H 0.4334 0.5246 0.2049 0.037 Uiso 1 1 calc R . . . .
C109 C 0.4508(10) 0.535(2) 0.1509(4) 0.035(3) Uani 1 1 d . . . . .
H10C H 0.4195 0.6401 0.1457 0.041 Uiso 1 1 calc R . . . .
H10D H 0.5136 0.5587 0.1571 0.041 Uiso 1 1 calc R . . . .
C111 C 0.3398(9) 0.405(2) 0.1087(4) 0.033(3) Uani 1 1 d . . . . .
H11C H 0.3273 0.3363 0.0865 0.040 Uiso 1 1 calc R . . . .
H11D H 0.3112 0.5129 0.1028 0.040 Uiso 1 1 calc R . . . .
C112 C 0.3016(9) 0.321(2) 0.1389(4) 0.032(3) Uani 1 1 d . . . . .
H11E H 0.2376 0.3214 0.1320 0.038 Uiso 1 1 calc R . . . .
H11F H 0.3211 0.2053 0.1414 0.038 Uiso 1 1 calc R . . . .
C122 C 0.0095(7) 0.4950(17) 0.3628(3) 0.034(3) Uani 1 1 d D U . . .
C124 C -0.0614(9) 0.510(2) 0.3882(4) 0.033(3) Uani 1 1 d . U . . .
H124 H -0.1141 0.4494 0.3757 0.040 Uiso 1 1 calc R . . . .
C126 C -0.0322(8) 0.241(2) 0.4225(4) 0.029(3) Uani 1 1 d . . . . .
C127 C 0.0352(9) 0.178(2) 0.4543(4) 0.030(3) Uani 1 1 d . . . . .
C128 C 0.0559(10) 0.019(2) 0.4657(5) 0.036(3) Uani 1 1 d . . . . .
H128 H 0.0253 -0.0726 0.4538 0.043 Uiso 1 1 calc R . . . .
C129 C 0.1248(11) -0.002(2) 0.4962(5) 0.042(4) Uani 1 1 d . . . . .
H129 H 0.1398 -0.1096 0.5051 0.051 Uiso 1 1 calc R . . . .
C130 C 0.1707(10) 0.134(3) 0.5130(4) 0.045(4) Uani 1 1 d . . . . .
H130 H 0.2164 0.1153 0.5332 0.054 Uiso 1 1 calc R . . . .
C131 C 0.1516(10) 0.297(2) 0.5012(4) 0.038(3) Uani 1 1 d . . . . .
H131 H 0.1827 0.3882 0.5131 0.046 Uiso 1 1 calc R . . . .
C132 C 0.0835(9) 0.319(2) 0.4705(4) 0.032(3) Uani 1 1 d . . . . .
C133 C 0.0474(10) 0.474(2) 0.4500(4) 0.037(3) Uani 1 1 d . . . . .
C136 C -0.0906(9) 0.687(2) 0.3951(4) 0.034(3) Uani 1 1 d . . . . .
H136 H -0.0379 0.7539 0.4048 0.040 Uiso 1 1 calc R . . . .
C137 C -0.1499(13) 0.686(3) 0.4240(5) 0.048(4) Uani 1 1 d . . . . .
H13A H -0.2013 0.6183 0.4152 0.072 Uiso 1 1 calc GR . . . .
H13B H -0.1677 0.7984 0.4282 0.072 Uiso 1 1 calc GR . . . .
H13C H -0.1177 0.6396 0.4468 0.072 Uiso 1 1 calc GR . . . .
C138 C -0.1386(11) 0.768(2) 0.3597(5) 0.041(3) Uani 1 1 d . . . . .
H13D H -0.1040 0.7558 0.3409 0.061 Uiso 1 1 calc GR . . . .
H13E H -0.1474 0.8850 0.3639 0.061 Uiso 1 1 calc GR . . . .
H13F H -0.1949 0.7143 0.3517 0.061 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O21 2.217(10) . ?
I1 N1 2.240(11) . ?
O10 C9 1.40(2) . ?
O10 C11 1.426(16) . ?
O21 C22 1.328(16) . ?
O23 C22 1.172(17) . ?
O34 C26 1.20(2) . ?
O35 C33 1.227(19) . ?
N1 C2 1.360(16) . ?
N1 C6 1.349(19) . ?
N7 C4 1.378(16) . ?
N7 C8 1.452(15) . ?
N7 C12 1.477(17) . ?
N25 C24 1.466(17) . ?
N25 C26 1.406(19) . ?
N25 C33 1.39(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.42(2) . ?
C4 C5 1.411(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(19) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.518(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.53(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C22 C24 1.589(17) . ?
C24 H24 0.9800 . ?
C24 C36 1.554(17) . ?
C26 C27 1.49(2) . ?
C27 C28 1.38(2) . ?
C27 C32 1.40(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.38(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.39(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.42(2) . ?
C31 H31 0.9300 . ?
C31 C32 1.35(2) . ?
C32 C33 1.498(19) . ?
C36 H36 0.9800 . ?
C36 C37 1.51(2) . ?
C36 C38 1.52(2) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
I2 O121 2.267(10) . ?
I2 N101 2.249(11) . ?
O110 C109 1.424(18) . ?
O110 C111 1.422(17) . ?
O121 C122 1.274(12) . ?
O123 C122 1.186(11) . ?
O134 C126 1.220(18) . ?
O135 C133 1.17(2) . ?
N101 C102 1.354(18) . ?
N101 C106 1.33(2) . ?
N107 C104 1.358(17) . ?
N107 C108 1.454(15) . ?
N107 C112 1.474(18) . ?
N125 C124 1.46(2) . ?
N125 C126 1.40(2) . ?
N125 C133 1.436(18) . ?
C102 H102 0.9300 . ?
C102 C103 1.390(18) . ?
C103 H103 0.9300 . ?
C103 C104 1.40(2) . ?
C104 C105 1.416(18) . ?
C105 H105 0.9300 . ?
C105 C106 1.384(18) . ?
C106 H106 0.9300 . ?
C108 H10A 0.9700 . ?
C108 H10B 0.9700 . ?
C108 C109 1.52(2) . ?
C109 H10C 0.9700 . ?
C109 H10D 0.9700 . ?
C111 H11C 0.9700 . ?
C111 H11D 0.9700 . ?
C111 C112 1.516(19) . ?
C112 H11E 0.9700 . ?
C112 H11F 0.9700 . ?
C122 C124 1.580(18) . ?
C124 H124 0.9800 . ?
C124 C136 1.51(2) . ?
C126 C127 1.492(18) . ?
C127 C128 1.36(2) . ?
C127 C132 1.41(2) . ?
C128 H128 0.9300 . ?
C128 C129 1.40(2) . ?
C129 H129 0.9300 . ?
C129 C130 1.37(3) . ?
C130 H130 0.9300 . ?
C130 C131 1.39(3) . ?
C131 H131 0.9300 . ?
C131 C132 1.39(2) . ?
C132 C133 1.49(2) . ?
C136 H136 0.9800 . ?
C136 C137 1.54(2) . ?
C136 C138 1.51(2) . ?
C137 H13A 0.9600 . ?
C137 H13B 0.9600 . ?
C137 H13C 0.9600 . ?
C138 H13D 0.9600 . ?
C138 H13E 0.9600 . ?
C138 H13F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O21 I1 N1 171.8(4) . . ?
C9 O10 C11 109.4(11) . . ?
C22 O21 I1 114.4(8) . . ?
C2 N1 I1 117.1(9) . . ?
C6 N1 I1 124.5(9) . . ?
C6 N1 C2 118.4(11) . . ?
C4 N7 C8 120.3(11) . . ?
C4 N7 C12 121.2(11) . . ?
C8 N7 C12 114.6(10) . . ?
C26 N25 C24 123.6(13) . . ?
C33 N25 C24 124.0(12) . . ?
C33 N25 C26 111.7(13) . . ?
N1 C2 H2 118.6 . . ?
N1 C2 C3 122.7(13) . . ?
C3 C2 H2 118.6 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(12) . . ?
C4 C3 H3 120.1 . . ?
N7 C4 C3 121.6(11) . . ?
N7 C4 C5 122.2(12) . . ?
C5 C4 C3 116.2(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(13) . . ?
C6 C5 H5 119.6 . . ?
N1 C6 C5 121.8(12) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
N7 C8 H8A 109.6 . . ?
N7 C8 H8B 109.6 . . ?
N7 C8 C9 110.4(11) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
O10 C9 C8 112.3(13) . . ?
O10 C9 H9A 109.1 . . ?
O10 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
O10 C11 C12 110.9(11) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
N7 C12 C11 109.4(12) . . ?
N7 C12 H12A 109.8 . . ?
N7 C12 H12B 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O21 C22 C24 109.6(10) . . ?
O23 C22 O21 128.5(12) . . ?
O23 C22 C24 121.7(12) . . ?
N25 C24 C22 110.4(11) . . ?
N25 C24 H24 106.5 . . ?
N25 C24 C36 114.9(10) . . ?
C22 C24 H24 106.5 . . ?
C36 C24 C22 111.5(10) . . ?
C36 C24 H24 106.5 . . ?
O34 C26 N25 125.4(16) . . ?
O34 C26 C27 129.3(14) . . ?
N25 C26 C27 105.3(14) . . ?
C28 C27 C26 130.7(16) . . ?
C28 C27 C32 120.0(17) . . ?
C32 C27 C26 109.3(13) . . ?
C27 C28 H28 120.8 . . ?
C29 C28 C27 118.5(17) . . ?
C29 C28 H28 120.8 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.0(15) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 H30 119.6 . . ?
C29 C30 C31 120.8(18) . . ?
C31 C30 H30 119.6 . . ?
C30 C31 H31 121.6 . . ?
C32 C31 C30 116.8(16) . . ?
C32 C31 H31 121.6 . . ?
C27 C32 C33 106.3(14) . . ?
C31 C32 C27 122.9(14) . . ?
C31 C32 C33 130.9(15) . . ?
O35 C33 N25 123.8(14) . . ?
O35 C33 C32 128.8(16) . . ?
N25 C33 C32 107.4(12) . . ?
C24 C36 H36 108.1 . . ?
C37 C36 C24 109.6(12) . . ?
C37 C36 H36 108.1 . . ?
C37 C36 C38 111.1(15) . . ?
C38 C36 C24 111.7(12) . . ?
C38 C36 H36 108.1 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N101 I2 O121 175.7(4) . . ?
C111 O110 C109 109.1(11) . . ?
C122 O121 I2 113.0(8) . . ?
C102 N101 I2 119.8(9) . . ?
C106 N101 I2 120.0(9) . . ?
C106 N101 C102 120.0(12) . . ?
C104 N107 C108 121.8(11) . . ?
C104 N107 C112 121.5(11) . . ?
C108 N107 C112 114.1(11) . . ?
C126 N125 C124 120.2(12) . . ?
C126 N125 C133 111.2(13) . . ?
C133 N125 C124 124.5(13) . . ?
N101 C102 H102 119.8 . . ?
N101 C102 C103 120.4(13) . . ?
C103 C102 H102 119.8 . . ?
C102 C103 H103 119.5 . . ?
C102 C103 C104 121.0(13) . . ?
C104 C103 H103 119.5 . . ?
N107 C104 C103 122.6(12) . . ?
N107 C104 C105 121.2(13) . . ?
C103 C104 C105 116.1(12) . . ?
C104 C105 H105 120.1 . . ?
C106 C105 C104 119.8(13) . . ?
C106 C105 H105 120.1 . . ?
N101 C106 C105 122.2(13) . . ?
N101 C106 H106 118.9 . . ?
C105 C106 H106 118.9 . . ?
N107 C108 H10A 109.6 . . ?
N107 C108 H10B 109.6 . . ?
N107 C108 C109 110.5(11) . . ?
H10A C108 H10B 108.1 . . ?
C109 C108 H10A 109.6 . . ?
C109 C108 H10B 109.6 . . ?
O110 C109 C108 110.8(13) . . ?
O110 C109 H10C 109.5 . . ?
O110 C109 H10D 109.5 . . ?
C108 C109 H10C 109.5 . . ?
C108 C109 H10D 109.5 . . ?
H10C C109 H10D 108.1 . . ?
O110 C111 H11C 109.1 . . ?
O110 C111 H11D 109.1 . . ?
O110 C111 C112 112.4(12) . . ?
H11C C111 H11D 107.9 . . ?
C112 C111 H11C 109.1 . . ?
C112 C111 H11D 109.1 . . ?
N107 C112 C111 111.6(12) . . ?
N107 C112 H11E 109.3 . . ?
N107 C112 H11F 109.3 . . ?
C111 C112 H11E 109.3 . . ?
C111 C112 H11F 109.3 . . ?
H11E C112 H11F 108.0 . . ?
O121 C122 C124 113.6(10) . . ?
O123 C122 O121 126.3(13) . . ?
O123 C122 C124 119.9(12) . . ?
N125 C124 C122 105.3(11) . . ?
N125 C124 H124 107.0 . . ?
N125 C124 C136 114.2(13) . . ?
C122 C124 H124 107.0 . . ?
C136 C124 C122 115.8(12) . . ?
C136 C124 H124 107.0 . . ?
O134 C126 N125 123.9(13) . . ?
O134 C126 C127 128.7(15) . . ?
N125 C126 C127 107.4(12) . . ?
C128 C127 C126 130.0(14) . . ?
C128 C127 C132 122.7(13) . . ?
C132 C127 C126 107.0(13) . . ?
C127 C128 H128 121.4 . . ?
C127 C128 C129 117.2(15) . . ?
C129 C128 H128 121.4 . . ?
C128 C129 H129 119.6 . . ?
C130 C129 C128 120.8(17) . . ?
C130 C129 H129 119.6 . . ?
C129 C130 H130 118.7 . . ?
C129 C130 C131 122.6(14) . . ?
C131 C130 H130 118.7 . . ?
C130 C131 H131 121.5 . . ?
C130 C131 C132 116.9(15) . . ?
C132 C131 H131 121.5 . . ?
C127 C132 C133 109.2(12) . . ?
C131 C132 C127 119.5(15) . . ?
C131 C132 C133 131.3(15) . . ?
O135 C133 N125 127.4(15) . . ?
O135 C133 C132 127.5(14) . . ?
N125 C133 C132 105.1(13) . . ?
C124 C136 H136 108.3 . . ?
C124 C136 C137 110.4(13) . . ?
C137 C136 H136 108.3 . . ?
C138 C136 C124 111.2(14) . . ?
C138 C136 H136 108.3 . . ?
C138 C136 C137 110.2(14) . . ?
C136 C137 H13A 109.5 . . ?
C136 C137 H13B 109.5 . . ?
C136 C137 H13C 109.5 . . ?
H13A C137 H13B 109.5 . . ?
H13A C137 H13C 109.5 . . ?
H13B C137 H13C 109.5 . . ?
C136 C138 H13D 109.5 . . ?
C136 C138 H13E 109.5 . . ?
C136 C138 H13F 109.5 . . ?
H13D C138 H13E 109.5 . . ?
H13D C138 H13F 109.5 . . ?
H13E C138 H13F 109.5 . . ?


_ins_header                      
;
TITL TIO-104_2_numabs_ana2 in I2 
REM I2 (#5 in standard setting)
CELL 1.54184  15.435579   7.966675  36.891780  90.0000 101.4293  90.0000
ZERR    8.00   0.000341   0.000213   0.000850   0.0000   0.0022   0.0000
LATT -2
SYMM -x, y,-z 
SFAC C H N O I
UNIT 176.00 192.00 24.00 40.00 8.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.533

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/pentane'
